Dichloromethane → HCID 18386111, compound

HRID 2298312Notes

Reaction equation

HRID 2298312 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11](SC)=[CH:10][CH:9]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[O:3]1.OO[S:29]([O-:31])=[O:30].[K+].Cl[CH2:34]Cl>CO>[CH3:26][C:2]1([CH3:1])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:29]([CH3:34])(=[O:31])=[O:30])=[CH:10][CH:9]=2)=[C:4]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[O:3]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 18385579HCID 18385579, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18386111HCID 18386111, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mg of 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-{4-(methylthio)-phenyl}-3(2H)-furanone (Example 72) in 10 ml dichloromethane and 2 ml methanol was stirred with 300 mg of OXONE at room temperature for 4 hours. The insoluble material was filtered off and the filtrate was washed with aqueous sodium bicarbonate. The organic layer was then concentrated under reduced pressure and was purified by column chromatography (ethylacetate) to give 45 mg of 2,2-dimethyl-4,5-di{4-(methylsulfonyl)phenyl}-3(2H)-furanone. mp: 245-257° C. NMR: δ1.60 (s, 6H), 3.08 (s, 3H), 3.10 (s, 3H), 7.50-7.53 (m, 2H), 7.79-7.82 (m, 2H), 7.94-8.00 (m, 4H). IR (cm−1): 2931, 1698, 1510, 1387, 1258, 1150, 960, 846, 770.

Workup

  1. filtrationThe insoluble material was filtered off
  2. washthe filtrate was washed with aqueous sodium bicarbonate
  3. concentrationThe organic layer was then concentrated under reduced pressure
  4. customwas purified by column chromatography (ethylacetate)

Sources & evidence

ORD record
ord-e3658c78d6b9493cbb67a9725d362990
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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